Calcium Chloride → trans-2-(5-Amino-3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxy-phenyl)-1,3-dithiolane

HRID 1684035Notes

Reaction equation

HRID 1684035 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:14]2[S:18][C@H:17]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[CH2:16][S:15]2)[CH:6]=[C:7]([N+:11]([O-])=O)[C:8]=1[O:9][CH3:10].[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Zn]>[NH2:11][C:7]1[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([C@H:14]2[S:18][C@H:17]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[CH2:16][S:15]2)[CH:6]=1

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 86750974trans-2-(3,4-Dimethoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Product 1

HCID 86750975trans-2-(5-Amino-3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxy-phenyl)-1,3-dithiolane

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Trans-2-(3,4-dimethoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane (2) (FIG. 20) (3.10 g, 6.84 mmole) was predissolved in 33 ml absolute ethanol. To this solution was added calcium chloride (0.721 g, 6.50 mmole) predissolved in 7 ml H2O followed by freshly activated zinc dust (10.0 g,195 mmole). The reaction was refluxed for 12 hours. The solid was removed by vacuum filtration through celite and was washed with ethyl acetate. The filtrate was washed with H2O, dried over MgSO4, and evaporated in vacuo to a white foam (2.52 g, 87%).

Workup

  1. temperatureThe reaction was refluxed for 12 hours
  2. customThe solid was removed by vacuum filtration through celite
  3. washwas washed with ethyl acetate
  4. washThe filtrate was washed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo to a white foam (2.52 g, 87%)

Sources & evidence

ORD record
ord-4ae30ea1d7234c1ca0c32e4ea68bea59
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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